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Electrophilic aromatic substitution

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Full-Text Articles in Physical Sciences and Mathematics

Synthesis Of Tenuifolin Via Intramolecular Nicholas Reaction, Sinisa Djurdjevic, James R. Green Oct 2014

Synthesis Of Tenuifolin Via Intramolecular Nicholas Reaction, Sinisa Djurdjevic, James R. Green

Chemistry and Biochemistry Publications

The synthesis of the Cinnamomum homosesquiterpenoid tenuifolin has been accomplished by way of an intramolecular Nicholas reaction of the [Co2(CO)6] complex of an alkyne-substituted biaryl for construction of the seven-membered ring. The cyclization features the reaction of a nonactivated arene ring with the propargyldicobalt cation to give the dibenzocycloheptyne-Co2(CO)6.


Bicatalytic Allylation–Cross-Metathesis Reactions As Γ-Carbonyl Cation Equivalents, Jake R. Henkie, Sugadar Dhaliwal, James R. Green Oct 2012

Bicatalytic Allylation–Cross-Metathesis Reactions As Γ-Carbonyl Cation Equivalents, Jake R. Henkie, Sugadar Dhaliwal, James R. Green

Chemistry and Biochemistry Publications

The products corresponding to the reactions of arenes and γ-carbonyl cations may be obtained by a one-pot, bicatalytic process involving InCl3-catalyzed arene allylation and cross metathesis with electron-deficient alkenes. The process is successful with electronically neutral and electron-rich arenes, and modestly Lewis basic donor groups are tolerated with an increase in InCl3 loading from 10 mol% to 15 mol%, and in one case, 20 mol%.